2-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene | 1474060-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene
• 英文别名: 2-[1-(3,4,5-Trimethoxyphenyl)ethenyl]thiophene；2-[1-(3,4,5-trimethoxyphenyl)ethenyl]thiophene
• CAS: 1474060-72-4
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: PGGAEVDPXGJNMF-UHFFFAOYSA-N

物化性质

• 沸点：
  395.1±37.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 7.0h， 生成 2-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-thiophene
  参考文献：
  名称：

  Combretastatin A-4含硫杂环衍生物：合成，抗增殖活性和分子对接研究

  摘要：

  合成了Combretastatin A-4激发的杂环衍生物，并评估了其对微管蛋白聚合和细胞增殖的生物学活性。在上述19种含硫化合物中，衍生物（Z）-4h和（Z）-4j在纤维素微管蛋白聚合抑制和抗增殖活性方面表现出令人关注的效果，六个不同的细胞系介于8和27 nM之间具有IC 50值。此外，in silico在微管蛋白的秋水仙碱/ CA-4结合位点内进行了对接研究，以了解我们产品与蛋白质靶标的相互作用。还以1–10 nM的浓度研究了对滤泡性淋巴瘤细胞的细胞周期的影响，表明发生了凋亡过程。

  DOI：

  10.1016/j.ejmech.2021.113275

文献信息

• Negishi Cross-Coupling Reaction as a Route to Isocombretastatins
  作者：Alexey Fedorov、Yulia Malysheva、Svetlana Buchvalova、Elena Svirshchevskaya、Valery Fokin

  DOI：10.1055/s-0033-1339334

  日期：——

  A series of isocombretastatins A has been synthesized by a new method based on the Negishi cross-coupling reaction in 19-84% yields. Five of the synthesized compounds exhibit high cytotoxic activity in nanomolar concentrations (IC50 = 1-100 nM) towards Jurkat, K562, Colo357, and A549 cell lines.
• Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit
  作者：Cong Viet Do、Abdelfattah Faouzi、Caroline Barette、Amaury Farce、Marie-Odile Fauvarque、Evelyne Colomb、Laura Catry、Odile Berthier-Vergnes、Marek Haftek、Roland Barret、Thierry Lomberget

  DOI：10.1016/j.bmcl.2015.11.010

  日期：2016.1

  Combretastatin A-4 and isocombretastatin A-4 derivatives having thiophenes or benzo[b]thiophenes instead of the B ring were prepared and evaluated for their in cellulo tubulin polymerization inhibition (TPI) and antiproliferative activities. The presence of the benzo[b]thiophene ring proved to have a crucial effect as most of the thiophene derivatives, except those having one methoxy group, were inactive to inhibit tubulin polymerization into microtubules. The influence of the attachment position was also studied: benzo[b]thiophenes having iso or cis 3,4,5-trimethoxystyrenes at position 2 were 12-30-fold more active than the 3-regioisomers for the TPI activity. Some of the novel designed compounds exhibited interesting anti-proliferative effects on two different cell lines. (C) 2015 Elsevier Ltd. All rights reserved.
• Combretastatin A-4 sulfur-containing heterocyclic derivatives: Synthesis, antiproliferative activities and molecular docking studies
  作者：Abdelfattah Faouzi、Alexandre Arnaud、Alexandre Bancet、Caroline Barette、Jordane Preto、Cong Viet Do、Lars Petter Jordheim、Zineb Bousfiha、Thi Thanh Binh Nguyen、Marion Verrière、Amaury Farce、Marie-Odile Fauvarque、Roland Barret、Thierry Lomberget

  DOI：10.1016/j.ejmech.2021.113275

  日期：2021.4

  Combretastatin A-4 inspired heterocyclic derivatives were synthesized and evaluated for their biological activities on tubulin polymerization and cell proliferation. Among the 19 described sulfur-containing compounds, derivatives (Z)-4h and (Z)-4j exhibited interesting in cellulo tubulin polymerization inhibition and antiproliferative activities with IC50 values for six different cell lines between

  合成了Combretastatin A-4激发的杂环衍生物，并评估了其对微管蛋白聚合和细胞增殖的生物学活性。在上述19种含硫化合物中，衍生物（Z）-4h和（Z）-4j在纤维素微管蛋白聚合抑制和抗增殖活性方面表现出令人关注的效果，六个不同的细胞系介于8和27 nM之间具有IC 50值。此外，in silico在微管蛋白的秋水仙碱/ CA-4结合位点内进行了对接研究，以了解我们产品与蛋白质靶标的相互作用。还以1–10 nM的浓度研究了对滤泡性淋巴瘤细胞的细胞周期的影响，表明发生了凋亡过程。